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CALGARY–"Not all those who wander are lost," says Brett Wilson, quoting J.R.R. Tolkien and setting the pace for an examination of Dragon No. 5 that's one part business, three parts psychoanalysis.

It's the kind of quote that telegraphs to the interviewer that this is not the moment to talk about oil and gas futures or investment banking deals or ROI. The citation is a daring, ask-me-anything come-on, quite in keeping with Wilson's on-air persona as the dragon with a heart on Dragons' Den, the guy who can fall for the tear-streaked emotional collapse of hopeful entrepreneurs seeking a farthing or two for their fragile business start-ups. The rich dragon – possibly the richest – who likes to say yes. The dragon who in a recent Facebook posting wrote: "Always kiss her like it's the first time, and the last time."

Why would he post that? "Someone may have been reading it," he says, tossing yet another emotional breadcrumb in the interviewer's path.

Of course, you will want to know who that "someone" is. But that comes later.

He's dressed in jeans, Wilson is. His hair is the longest it's been since he was in high school. His dog Maya is padding behind him, looking for love, just like his master. The handsome Mount Royal house is packed with Saskatchewan art, testament to Wilson's Prairie roots. There's a Joe Fafard sculpture of Ernst Lindner in the living room. There are Ernst Lindner paintings everywhere, including an uncharacteristic Lindner of daisies being clutched between a pair of startlingly full breasts.

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Is this not painting a picture of a mover and shaker in your mind?

The bulk of Wilson's wealth comes from oil and gas, a story that wends its way from investment banker McLeod Young Weir to the self-named start-up Wilson Mackie to the building of FirstEnergy Corp. Anyone wanting to understand how profitable this trajectory was for Wilson, hear him say this: "Calgary was always considered a place where you could airplane bank." Translation: the money was run by visiting investment bankers from Toronto, or, just as bad, New York.

"There is nothing that oilmen hate more than dialling 416 or 212 and asking for help," Wilson continues. "It's such an arrogant perspective." One memory: he's working for MYW out of Calgary. His assistant pops her head in the door. "Toronto is on the phone," she says. "Tell them Calgary's in the washroom," he replies.

So FirstEnergy was established in 1993 as an investment dealer catering exclusively to the energy sector. "We could have been called Only Energy," says Wilson of the company's focus. He became fabulously wealthy.

We could talk about the money. Or we could talk about the price he paid in making it. "I got absorbed into that work-money, work-money cycle, deal, deal, deal at McLeod," he says. "Then when I started my own business, each hour I wasn't working was an expensive hour."

His marriage started to teeter. "The worse my marriage was the more time I spent at the office. The more time I spent at the office, the worse my marriage was."

In a special Dragons' Den episode airing Wednesday, the back stories of the dragons themselves are lightly told. Wilson speaks of his divorce.

He doesn't talk about checking himself into an addiction research program. "I thought it was workaholism," he says "but as it turns out we went back and peeled back all of the layers of the onion and got back to Brett the boy at 4, 6, 8, 10, 12. There were a few issues ... some speed bumps ... It was a powerful experience."

He says that any talk of an alcohol dependency is not accurate. "There was no dependency on alcohol whatsoever," he responds. "What there was, was an inappropriate style of drinking." He defines "inappropriate" as binge drinking. "It wasn't like I just sat down and hammered drinks. But if the party went on until three in the morning I was probably drunk. If it went on to 11 I was probably tipsy ... I would just drink until the party was over."

Depression? "Absolutely. I joke about seeing a list of the 12 signs of clinical depression and going through the list and nine of them were clearly me and the other three, well, I was still in denial."

One day in 2001 his lawyer called. The paperwork on the divorce had been finalized. "I closed the file and said to my secretary you can put the divorce file away. An hour later I get a call." Here he mimics his own self calling out to his secretary: "Wendy, can you open another file?" Wendy replies, "What is it?" Wilson's response: "Call it cancer."

Brett Wilson's friend Warren Spitz talks about how Wilson pushed the reset button on life. Cancer – prostate cancer in Wilson's case – will do that to you. Divorce will do that to you. A determination to fix the frailty of a relationship with three children will do that to you. "The cost of success was my health, my family, my marriage," says Wilson. "It wasn't worth it."

Wilson stepped down as chair of FirstEnergy in January, his business interests focused wholly now on Prairie Merchant Corp., his private investment company. His interest in the Diamond Jaxx is in there (Tennessee: baseball); as is his stake in Derby County, the U.K. football club he calls the "Saskatchewan Roughriders of the Midlands." He's still hoping for a piece of the Nashville Predators. There's an advertising agency. A fitness franchise. A divorce solutions company. Real estate. We could go on.

But the baseline in Brett Wilson's reset life is No. 1, his kids, and No. 2, philanthropy. "He's not just walking around trying to give people money," says Spitz of Wilson's philanthropic endeavours. "He's trying to help people get on their feet and stay on their feet."

Wilson is inexhaustible when it comes to causes. Keith Harradence, a friend from Wilson's undergrad days at the University of Saskatchewan, recounts a climb up Kilimanjaro to raise money for Alzheimer's research. Climbers were compelled to raise $10,000. "A week before the climb he hadn't had a chance to do any money raising," says Harradence. "We started the climb – it was a six-day climb. We get news two-thirds up the mountain that the 800 or so letters that he had personally signed before departing had raised over $300,000. That's just the way he is, right? Brett in a week could raise in excess of $300,000."

Dragons' Den plays in to that. On the surface it exposes Brett Wilson's heart, which Warren Spitz says is three times too big sometimes. He means that in the nicest way.

Sometimes other dragons have mocked Wilson, as they did when he invested in the Aerial Angels, a travelling acrobatic troupe. "They made fun of it, on national TV," says Wilson. "My girlfriend was upset ... She said you don't look like you care ... I said if I valued their opinions I would be deeply concerned."

Yes, there's a sting there. Wilson is well aware of how soft he can sometimes appear on television, especially against the caustic pronouncements of Kevin O'Leary. He says the diligent editing of the show makes him appear kinder than he is on occasion. He says he asks a bazillion questions, possibly deemed tedious by the editing team.

"I've never seen them use the core business question I ask, which is how much money and how much time have you got invested in the business? I've asked that of everyone I've ever invested in. I don't think it has ever made it to TV."

When he auditioned he was told he wasn't mean enough. "I said, look, if `mean' means being a prick, don't ask me back. I'm not interested. I'm not going to `mean up' for the show."

That's what he said then.

Today he appears interested in sharpening his elbows. "Each year I get tougher and ruder but not to the people coming on the show. Just to the other dragons." When he calls Kevin O'Leary a "moronic outlier of capitalism," he says he intends it in a friendly, spirited way.

The other dragons need him. Wilson is by far the largest deal doer. "He doesn't think enough deals are done. He told me that," says Keith Harradence, who had dinner with Wilson shortly after he accepted the dragon role. Wilson has done more than 15 deals since he signed on, committing between $3.5 million and $4 million in capital.

Then there's the issue of equity. "If you look at some of the advertising you'd think it was the Kevin O'Leary and friends show," Wilson says. He took up the point with the CBC. "I just said, that stops. No more. It's Brett and Kevin and Robert and Jim and Arlene. Equal billing."

There's ego at play, no surprise.

And, with Wilson at least, no guile.

The day is drawing to a close.

Is he happy? "For what it's worth," Wilson replies, "happiness jumped a notch when I came out of the Hoffman Institute last December."

Whoa.

With Brett Wilson, there are no uncomplicated answers. This is the third time in our encounter that he has returned to the therapeutic peeling of the onion, the getting back to unnamed issues unresolved, in this case checking into an eight-day intensive residential program that explores the first 12 years of childhood. "What they do is they explore the negative patterns in your life," he offers. "The whole premise is built around the concept of negative love ... The negative patterns in your life that came as a result of the ones who loved you."

He says the program has helped enormously. You get the sense all the emotional tremors in Brett Wilson's life run close to the surface. What were the issues in childhood?

"Let's just assume I've always had speed bumps," he says. The Hoffman, a place that will cause eye rolling and near cult accusations from skeptics, helped, and it's unconventional to hear such admissions in business quarters. "A lot of this shit, I realized, is their shit. It's not my shit," says Wilson, sounding very unlike his dragon persona.

Is he happy in love? On a side table in the living room there's a framed pen and ink etching of a fire-breathing dragon. "That's a McLachlan," he says, meaning the singer Sarah, who signed the artwork with love to Brett on his 50th birthday.

"We spend time together," he says when asked if they are still dating. "Anyone who saw us at the Olympics would know that we spend time together."

Read into that what you will. There is more interesting territory to explore, deeper crevices. Wilson is in the process of writing, with a ghostwriter, the first of what he sees as a number of books. He's grappling with how candid he will be. He knows he can be an inspiration to others. He asks that we go off the record. Brett Wilson is still thinking about how much he wants the world to know.

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